I have always said that if you can’t sleep then you’re not “hiking.” You’re “enduring.” And that’s seldom what I’m seeking. So I have a 30-degree bag that I carry even when it’s probably overkill, and I use a torso-length Thermarest on top of a CC foam pad. I’m probably going to break down and buy a NeoAir soon, to try it out. (Oh, and I’ve recently been schlepping a Klymit X-pillow, which is by a large margin the best inflatable pillow I’ve found.)
I’m with you on the hammock. Some of the most comfortable nights I’ve spent in the backcountry were in hammocks. But I find them annoying above treeline. So as a “works essentially anywhere” solution I use a pyramid shelter. I definitely still do the hammock thing, though. Weight-wise they’re comparable with a 2P pyramid, so it’s no loss for me.
My other luxury item is a real fixed-blade knife, which I mention because you are considering one. Heavy as hell, I know, but I had a bad experience once in the worst possible conditions- 32F and raining- during which I got thoroughly soaked and miserable and my Leatherman Squirt simply was not up to the task of helping me produce useable kindling. What can I say? I’m scarred. I carry a real knife. The only time I’ve carried a saw is when I’m out with my daughter- a little Bahco Laplander. For her hiking is All About The Fire so I need to keep it fed (in established designated sites). Otherwise, my knife is more than ideal for the tiny twig fires that I otherwise indulge in on occasion. I do carry a (pretty foolproof) magnesium firestarter as a backup to my Bic, too. That’s the only redundant equipment I carry.
I think your raingear policy is very reasonable.
I will say, though, that I REALLY don’t worry about “getting lost.” I should knock wood or something, but I’m one of those guys who simply doesn’t understand how someone gets lost enough to need survival equipment, unless they’ve lost their map or something, which should never happen. Situations like my soaking, above, yes, but not lost. Or hurt, yes, but not lost. And mind you I’ve been to some pretty out-there places, though granted not many of the truly challenging terrains like featureless plains.
So if you’re truly shaky on land navigation, sure, plan accordingly. Otherwise I wouldn’t obsess about it. Even then I long ago decided that so long as I had a fixed blade knife, a pot, and a reliable way to start a fire that I’d at least survive in (almost) any conditions until I started starving, which takes a while. Injury, of course, impacts this negatively, but I already carry all of that gear.